2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4S,5S)-2,2-dimethyl-5-[(phen ylmethoxy)methyl]-1,3-dioxolan-4-yl]-, methyl ester, (2Z,5S)-

Base Information

• Chemical Name: 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4S,5S)-2,2-dimethyl-5-[(phen ylmethoxy)methyl]-1,3-dioxolan-4-yl]-, methyl ester, (2Z,5S)-
• CAS No.: 562823-65-8
• Molecular Formula: C26H42O6Si
• Molecular Weight: 478.701
• Mol file: 562823-65-8.mol

Synonyms:

Chemical Property of 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4S,5S)-2,2-dimethyl-5-[(phen ylmethoxy)methyl]-1,3-dioxolan-4-yl]-, methyl ester, (2Z,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4S,5S)-2,2-dimethyl-5-[(phen ylmethoxy)methyl]-1,3-dioxolan-4-yl]-, methyl ester, (2Z,5S)-

There total 14 articles about 2-Hexenoic acid, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(4S,5S)-2,2-dimethyl-5-[(phen ylmethoxy)methyl]-1,3-dioxolan-4-yl]-, methyl ester, (2Z,5S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl bromide (100-39-0) → (Z)-(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester (562823-65-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / NaH / dimethylformamide / 4 h / 23 °C

2: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 2 h / 23 °C

3: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

4: 71 percent / tetrahydrofuran / 3 h / -78 °C

5: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

6: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

7: NaOH / tetrahydrofuran; H₂O / 14 h / 0 °C

8: imidazole / dimethylformamide / 18 h / 23 °C

9: diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3: Dess-Martin oxidation / 4: Brown's allylboration;

DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate (256494-25-4) → (Z)-(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester (562823-65-8)

Guidance literature:

Multi-step reaction with 12 steps

1: AD mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 0 °C

2: 92 percent / PPTS / acetone / 5 h / 23 °C

3: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

4: 69 percent / NaH / dimethylformamide / 4 h / 23 °C

5: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 2 h / 23 °C

6: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

7: 71 percent / tetrahydrofuran / 3 h / -78 °C

8: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

9: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

10: NaOH / tetrahydrofuran; H₂O / 14 h / 0 °C

11: imidazole / dimethylformamide / 18 h / 23 °C

12: diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; AD-mix-α; lithium borohydride; methanesulfonamide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 6: Dess-Martin oxidation / 7: Brown's allylboration;

DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (562823-71-6) → (Z)-(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester (562823-65-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

2: 71 percent / tetrahydrofuran / 3 h / -78 °C

3: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

5: NaOH / tetrahydrofuran; H₂O / 14 h / 0 °C

6: imidazole / dimethylformamide / 18 h / 23 °C

7: diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Dess-Martin oxidation / 2: Brown's allylboration;

DOI:10.1016/S0040-4039(03)00744-5

upstream raw materials:

diazomethane

benzyl bromide

(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate

2-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde

Downstream raw materials:

(2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester

Refernces